Acetone → 2,2-Di-(t-Octylperoxy) Propane

HRID 1605613

Reaction equation

[CH3:1][C:2]([CH3:4])=[O:3].[CH3:5][C:6]([O:13][OH:14])([CH3:12])[CH2:7][C:8]([CH3:11])([CH3:10])[CH3:9].S(=O)(=O)(O)O>CCCCC>[C:2]([O:3][O:13][C:6]([O:14][O:13][C:6]([CH2:7][C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:12])[CH3:5])([CH3:12])[CH3:5])([CH2:7][C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:4])[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a jacketed reactor was charged 7.0g. (0.12 mole) of acetone, 39.2g. (0.24 mole) of 1,1,3,3-tetramethylbutyl hydroperoxide (89.7% assay) and 120 ml. of pentane. To the vigorously stirred solution at 0°C was added 16g. of 77% sulfuric acid over a period of 30 minutes and the reaction mixture was allowed to stir at 0°C for 4 hours. The pentane layer was then separated, washed with water, then aqueous 10% KOH solution and finally with water to neutral and was dried over anhyd. MgSO4. After separation of the desiccant and vacuum stripping, 21.3g. (53.1% of theory, uncorr.) of liquid remained which had an "active oxygen" content of 8.66% (theory, 9.64%). Hence, the assay was 90% and the corrected yield was 47.8%. An infrared spectrum of the product showed no O--H or C=O bands but showed a strong OO band at 860 cm-1.

Workup

additionTo a jacketed reactor was charged 7.0g
customThe pentane layer was then separated
washwashed with water
dry with materialaqueous 10% KOH solution and finally with water to neutral and was dried over anhyd
customAfter separation of the desiccant and vacuum stripping, 21.3g

Sources & evidence

ORD record: ord-c0211e4f19ee41d59a436bc231c8a2a3
Source dataset: uspto-grants-1976_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03950432

Linked notes

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